Journal of the Chemical Society. Perkin transactions I p. 3245 - 3251 (1991)
Update date:2022-07-29
Topics:
Hunter, Gordon A.
McNab, Hamish
Monahan, Lilian C.
Blake, Alexander J.
Alkylation of 1-substituted 1H-pyrrol-3(2H)-ones 1 in the presence of base generally gives a mixture of O-alkylated 3, C,O-dialkylated 4 and C,C-dialkylated 5 products.The proportion of C-alkylation is increased by the use of a soft alkylating agent (e.g. iodomethane) and a solvent of l ow polarity (e.g.THF), whereas O-alkylation is favoured by hard alkylating agents (e.g. methyl toluene-p-sulphonate), and dipolar aprotic solvents (e.g. dimethylimidazolidinone).These latter conditions give a good preparative route to a wide range of 1-substituted and 1,2-disubstituted 3-alkoxypyrroles 3 (65-90percent yield).The X-ray crystal structure of 1-tert-butyl-3-methoxy-2-phenylpyrrole 22 is reported.
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